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Related Concept Videos

Five-Membered Heterocyclic Aromatic Compounds: Overview01:13

Five-Membered Heterocyclic Aromatic Compounds: Overview

5.9K
Heterocyclic aromatic compounds are cyclic compounds that are aromatic and have one or more heteroatoms—atoms other than carbon, in the ring. Depending upon the number of atoms present in the ring, they can be either five or six-membered. Examples of five-membered heterocyclic aromatic compounds include pyrrole, furan, thiophene, and imidazole. Pyrrole consists of one nitrogen atom having one lone pair of electrons. Furan and thiophene have one oxygen and one sulfur heteroatom,...
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Basicity of Heterocyclic Aromatic Amines01:25

Basicity of Heterocyclic Aromatic Amines

7.1K
Heterocyclic amines, where the N atom is a part of an alicyclic system, are similar in basicity to alkylamines. Interestingly, the heterocyclic amine having a nitrogen atom as part of an aromatic ring has much less basicity than its corresponding alicyclic counterpart. For this reason, as presented in Figure 1, piperidine (pKb = 2.8) is significantly more basic than pyridine (pKb = 8.8).
7.1K
Aromatic Hydrocarbon Cations: Structural Overview01:18

Aromatic Hydrocarbon Cations: Structural Overview

4.1K
Cycloheptatriene is a neutral monocyclic unsaturated hydrocarbon that consists of an odd number of carbon atoms and an intervening sp3 carbon in the ring. The three double bonds in the ring correspond to 6 π electrons, which is a Huckel number, and therefore satisfies the criteria of 4n + 2 π electrons. However, the intervening sp3 carbon disrupts the continuous overlap of p orbitals. As a result, cycloheptatriene is not aromatic.
Removing one hydrogen from the intervening CH2 group...
4.1K
Stability of Substituted Cyclohexanes02:30

Stability of Substituted Cyclohexanes

16.7K
This lesson discusses the stability of substituted cyclohexanes with a focus on energies of various conformers and the effect of 1,3-diaxial interactions.
The two chair conformations of cyclohexanes undergo rapid interconversion at room temperature. Both forms have identical energies and stabilities, each comprising equal amounts of the equilibrium mixture. Replacing a hydrogen atom with a functional group makes the two conformations energetically non-equivalent.
For example, in...
16.7K
Criteria for Aromaticity and the Hückel 4n + 2 Rule01:20

Criteria for Aromaticity and the Hückel 4n + 2 Rule

14.4K
Like benzene, cyclobutadiene and cyclooctatetraene are cyclic compounds with alternate single and double bonds. However, their chemical behavior differs from benzene, as they are unstable and not aromatic. So, what are the structural characteristics of unsaturated compounds categorized as aromatic?  
For the first time, Eric Hückel, a German chemical physicist, derived a set of structural features for a compound to be classified as aromatic. This is now known as Hückel’s rule or the 4n +...
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Nomenclature of Alkynes02:39

Nomenclature of Alkynes

22.4K
Alkynes are unsaturated hydrocarbons characterized by the presence of carbon-carbon triple bonds and have a general formula CnH2n-2. The nomenclature of alkynes follows a set of rules similar to alkanes and alkenes; however, alkynes bear the suffix "-yne" instead of "-ane" or "-ene." There are two approaches to naming alkynes:
22.4K

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Efficient Construction of Drug-like Bispirocyclic Scaffolds Via Organocatalytic Cycloadditions of α-Imino γ-Lactones and Alkylidene Pyrazolones
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Efficient Construction of Drug-like Bispirocyclic Scaffolds Via Organocatalytic Cycloadditions of α-Imino γ-Lactones and Alkylidene Pyrazolones

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Studies on Metastable Heterocycles: 2-Formyl-3-methylene-1-pyrroline.

Aleksandras Lotuzas1, Ashley A Michel1, Patrick G Harran1

  • 1Department of Chemistry and Biochemistry, University of California-Los Angeles, 607 Charles E. Young Drive East, Los Angeles, California 90095-1569, United States.

Organic Letters
|March 10, 2026
PubMed
Summary

A novel Staudinger-based synthesis yields a stable precursor for 2-formyl-3-methylene-1-pyrroline. This aldehyde, generated in situ, participates in various reactions, including a unique dimerization to form pyrrolo-pyrroline scaffolds.

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Synthesis of pH Dependent Pyrazole, Imidazole, and Isoindolone Dipyrrinone Fluorophores using a Claisen-Schmidt Condensation Approach
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Synthesis of pH Dependent Pyrazole, Imidazole, and Isoindolone Dipyrrinone Fluorophores using a Claisen-Schmidt Condensation Approach

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Syntheses, Crystallization, and Spectroscopic Characterization of 3,5-Lutidine N-Oxide Dehydrate
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Syntheses, Crystallization, and Spectroscopic Characterization of 3,5-Lutidine N-Oxide Dehydrate

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Synthesis of pH Dependent Pyrazole, Imidazole, and Isoindolone Dipyrrinone Fluorophores using a Claisen-Schmidt Condensation Approach
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Syntheses, Crystallization, and Spectroscopic Characterization of 3,5-Lutidine N-Oxide Dehydrate
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Syntheses, Crystallization, and Spectroscopic Characterization of 3,5-Lutidine N-Oxide Dehydrate

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Area of Science:

  • Organic Chemistry
  • Synthetic Chemistry
  • Medicinal Chemistry

Background:

  • Pyrroline derivatives are important scaffolds in medicinal chemistry.
  • Efficient synthesis of functionalized pyrrolines remains a challenge.

Purpose of the Study:

  • To develop a Staudinger-based synthesis for a stable acylal precursor to 2-formyl-3-methylene-1-pyrroline.
  • To explore the reactivity of the in situ generated aldehyde.

Main Methods:

  • Staudinger reaction for precursor synthesis.
  • Acetyl transfer to phenoxide.
  • In situ generation and characterization of the target aldehyde.
  • Exploration of reactions including nucleophilic substitution, cycloadditions, and Lewis acid-base-mediated dimerization.

Main Results:

  • A stable acylal precursor to 2-formyl-3-methylene-1-pyrroline was successfully synthesized.
  • The target aldehyde was generated in situ and characterized in solution.
  • The aldehyde underwent diverse reactions, including nucleophilic substitution and cycloadditions.
  • An unprecedented Lewis acid-base-mediated dimerization was achieved, yielding pyrrolo-pyrroline scaffolds.

Conclusions:

  • A versatile synthetic route to a key pyrroline intermediate has been established.
  • The in situ generated aldehyde is a valuable synthon for further chemical transformations.
  • The discovery of the pyrrolo-pyrroline scaffold formation opens new avenues in heterocyclic chemistry.